DE2846438A1 - Verfahren zur herstellung von cyanazofarbstoffen - Google Patents
Verfahren zur herstellung von cyanazofarbstoffenInfo
- Publication number
- DE2846438A1 DE2846438A1 DE19782846438 DE2846438A DE2846438A1 DE 2846438 A1 DE2846438 A1 DE 2846438A1 DE 19782846438 DE19782846438 DE 19782846438 DE 2846438 A DE2846438 A DE 2846438A DE 2846438 A1 DE2846438 A1 DE 2846438A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- hydrogen
- copper
- dyes
- aralkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000975 dye Substances 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- -1 alkali metal cyanide Chemical class 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 10
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910004013 NO 2 Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003799 water insoluble solvent Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- LEKPFOXEZRZPGW-UHFFFAOYSA-N copper;dicyanide Chemical compound [Cu+2].N#[C-].N#[C-] LEKPFOXEZRZPGW-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 description 1
- FDODVZVWGKVMBO-UHFFFAOYSA-N cyclohex-2-ene-1,4-diol Chemical compound OC1CCC(O)C=C1 FDODVZVWGKVMBO-UHFFFAOYSA-N 0.000 description 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Coloring (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782846438 DE2846438A1 (de) | 1978-10-25 | 1978-10-25 | Verfahren zur herstellung von cyanazofarbstoffen |
| US06/080,842 US4269770A (en) | 1978-10-25 | 1979-10-01 | Process for the preparation of cyanoazo dyestuffs |
| GB7936555A GB2034736B (en) | 1978-10-25 | 1979-10-22 | Process for the preparation of cyanaozo dyestuffs |
| CH950179A CH643868A5 (de) | 1978-10-25 | 1979-10-23 | Verfahren zur herstellung von cyanazofarbstoffen. |
| IT7926729A IT7926729A0 (it) | 1978-10-25 | 1979-10-23 | Procedimento per la preparazione di coloranti cianazoici. |
| JP13604079A JPS5558255A (en) | 1978-10-25 | 1979-10-23 | Manufacture of cyanoazo dyestuff |
| FR7926420A FR2439806A1 (fr) | 1978-10-25 | 1979-10-24 | Procede de production de colorants cyanazoiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782846438 DE2846438A1 (de) | 1978-10-25 | 1978-10-25 | Verfahren zur herstellung von cyanazofarbstoffen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2846438A1 true DE2846438A1 (de) | 1980-05-08 |
| DE2846438C2 DE2846438C2 (US07223432-20070529-C00017.png) | 1987-05-07 |
Family
ID=6053080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782846438 Granted DE2846438A1 (de) | 1978-10-25 | 1978-10-25 | Verfahren zur herstellung von cyanazofarbstoffen |
Country Status (7)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4315857A (en) * | 1979-07-20 | 1982-02-16 | Sandoz Ltd. | Process for the synthesis of azobenzene compounds having a cyano group in one or both of the ortho positions of the diazo component radical |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3003012A1 (de) * | 1980-01-29 | 1981-07-30 | Bayer Ag, 5090 Leverkusen | Azofarbstoffe sowie deren herstellung und verwendung zum faerben von synthesefasern |
| EP0038615A3 (en) * | 1980-04-03 | 1981-11-04 | Imperial Chemical Industries Plc | Disperse monoazo dyes |
| US4487719A (en) * | 1982-04-14 | 1984-12-11 | Eastman Kodak Company | Azo dyes from substituted 3-amino-pyridines with aniline, tetrahydroquinoline and benzomorpholine couplers |
| DE3705223A1 (de) * | 1986-07-30 | 1988-02-04 | Bayer Ag | Azofarbstoffe |
| DE3708714A1 (de) * | 1987-03-18 | 1988-09-29 | Bayer Ag | Azofarbstoffe |
| US5194598A (en) * | 1987-10-24 | 1993-03-16 | Bayer Aktiengesellschaft | Azo dyestuffs in which the coupling component contains an N,N-bis(alkoxy carbonylalkyl) substituent |
| DE3736088A1 (de) * | 1987-10-24 | 1989-05-03 | Bayer Ag | Azofarbstoffe |
| ES2135701T3 (es) * | 1995-02-27 | 1999-11-01 | Goran Bernhardsson | Estructura de suelo con medios de canal multiple. |
| DE19858997A1 (de) | 1998-12-21 | 2000-06-29 | Dystar Textilfarben Gmbh & Co | Thermomigrierechte Azofarbstoffe |
| TW200704718A (en) * | 2005-06-09 | 2007-02-01 | Clariant Int Ltd | Disperse azo dyes and mixtures comprising these disperse azo dyes |
| JP2016526055A (ja) * | 2013-04-27 | 2016-09-01 | ダウ グローバル テクノロジーズ エルエルシー | Ｌｃｄのカラーフィルタに使用されるアゾ染料 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1290915B (de) | 1966-02-17 | 1969-03-20 | Bayer Ag | Verfahren zum Faerben und Bedrucken von Fasermaterialien aus aromatischen Polyestern und Celluloseacetaten |
| US3627752A (en) | 1968-01-19 | 1971-12-14 | Cossella Farbwerke Mainkur Ag | Water-insoluble monoazo dyestuffs |
| DE2134896A1 (de) * | 1971-07-13 | 1973-02-01 | Basf Ag | Verfahren zur herstellung von cyangruppenhaltigen azofarbstoffen |
| GB1438374A (en) | 1972-08-16 | 1976-06-03 | Eastman Kodak Co | Preparation of azo dompounds |
| DE2310745C3 (de) * | 1973-03-03 | 1981-11-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Azoverbindungen |
| DE2610675C3 (de) | 1976-03-13 | 1979-05-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Cyanazofarbstoffen |
| GB1578732A (en) | 1976-05-28 | 1980-11-05 | Ici Ltd | Process for the manufacture of cyano azo dyes |
| GB1578731A (en) | 1976-05-28 | 1980-11-05 | Ici Ltd | Process for the manufacture of cyano azo dyes |
-
1978
- 1978-10-25 DE DE19782846438 patent/DE2846438A1/de active Granted
-
1979
- 1979-10-01 US US06/080,842 patent/US4269770A/en not_active Expired - Lifetime
- 1979-10-22 GB GB7936555A patent/GB2034736B/en not_active Expired
- 1979-10-23 CH CH950179A patent/CH643868A5/de not_active IP Right Cessation
- 1979-10-23 IT IT7926729A patent/IT7926729A0/it unknown
- 1979-10-23 JP JP13604079A patent/JPS5558255A/ja active Granted
- 1979-10-24 FR FR7926420A patent/FR2439806A1/fr active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4315857A (en) * | 1979-07-20 | 1982-02-16 | Sandoz Ltd. | Process for the synthesis of azobenzene compounds having a cyano group in one or both of the ortho positions of the diazo component radical |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2439806B1 (US07223432-20070529-C00017.png) | 1984-10-19 |
| FR2439806A1 (fr) | 1980-05-23 |
| US4269770A (en) | 1981-05-26 |
| DE2846438C2 (US07223432-20070529-C00017.png) | 1987-05-07 |
| GB2034736A (en) | 1980-06-11 |
| GB2034736B (en) | 1983-05-11 |
| JPS5558255A (en) | 1980-04-30 |
| JPS6318627B2 (US07223432-20070529-C00017.png) | 1988-04-19 |
| IT7926729A0 (it) | 1979-10-23 |
| CH643868A5 (de) | 1984-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |